Revised Plot Synopsis for NotAB

One paragraph = one Chapter

Chapters alternate her/his

First third: opens with retirement party for Vanessa. Lots of discussion of who is going to stay, who is thinking of moving on, where they are going. At least one person who arrived even later than Vanessa and was working as a contractor spends time telling Vanessa his strategy (low run rate, high asset, periodic short term gigs at high compensation).

Zach discusses with Kara whether this is something she finds appealing. Rambling discussion about children, lifestyle, goals: it is clear to the reader but apparently not to Zach that Kara is not at all keen on children. While Zach clearly wants to have a family and children and make them the center of his life, that is still “some day”; he hasn’t committed to doing that right now. Kara is emphatic he/they do not have enough to even think about retirement. Her numbers for at what point she would be willing to think about retirement are shocking to him, and in this pause she reminds him that he’s been talking about wanting to do a startup of his own. That gives him a positive goal that does not require him to think about whether Kara can be part of his future vision of a family with children. Kara is relieved that the pressure to tell him she doesn’t ever want to have children is off. He contacts friends. They start the process.

Vanessa’s friends and family have reservations about her plans over the long haul. When she says what the contractor told her, they decide to perceive her retirement as Not Really Retirement. She is a little puzzled, and talks it over with her mother. Mom tells her about the back and forth that she has had with dad over the years. Mom is okay with whatever she wants to do, but thinks it is important that Vanessa not just do Nothing, but pursue goals that she finds satisfying to her, whether they pay or not. Also, when are you getting married.

Zach’s startup initially does well, but does not monetize well. They pivot in order to monetize with a corporate market they did not anticipate (disintermediating Xerox as a document company). Hugely stressful period between angel/seed and Series A funding. Long hours. Unable to think about anything else. Kara wants more from him than he has to give and he ignores her, yells at her, and suggests she find someone else if he’s not a good enough boyfriend for her. She thinks it over and moves out; it takes him a few days to even notice she is gone. Lots of pissy friends.

Vanessa settles into a routine: exercise, some volunteer work, time with friends, babysitting children of friends so they can have date nights. After the first month or two, she starts arranging her socializing around walks, hikes, cultural outings (museums, cheap concerts) instead of around dinners out with a lot of drinking. She’s doing this to manage the calories and the cost; her friends are pretty happy with having someone organizing something other than the same old same old. She signs up to take some business classes at a Seattle College, and talks to her sister-in-law in some detail about the contracting plan. She gets in touch with the guy at the party and he puts her in touch with some other people. Nothing happens right away.

Second third: The pivot is successful. The concept has worked and they have a substantial and growing income stream from corporate clients who love their document indexing and management subscription service, that works in any cloud and has good security through browser access, downloadable application for Mac or PC, and mobile apps. There is a huge and growing list of bugs and desired new features (new document types and new accessing/searching schemes). They have hired more people, but they are going to need a lot more money and much more sophisticated management to really succeed. The original partners consider their options, and accept a buyout plan from a really huge company in a related space (Oracle, IBM, Xerox, mumble, conceivably Deloitte). Each of the partners will walk away with 20+ million dollars as long as they commit to a 24 month transition plan. They will no longer be managing the company, but will be focused on the architecture, and working with a team to beat the bugs into submission and get some new document types integrated. Zach’s hours will go down but more importantly, the stress is drastically reduced.

Vanessa’s schedule is now full, and she has been traveling some: staying at hostels, hiking around the SW, etc. When Zach asks her to go out for a celebratory dinner when the deal that buys him out is completed, she is not currently seeing anyone seriously, and she’s curious what has been going on with him. She is peripherally aware of the Kara/Zach drama, in which Kara’s side has been painting him as verbally abusive and a terrible boyfriend, Kara herself has basically taken the position: I Have No Idea What Happened It’s Like He Was A Different Person I Hope He’s OK. Zach’s side has been quiet, with individuals shrugging and saying, what did she expect, it was a startup. When she sees Zach, he is exhausted and detached, sort of going through the motions of the celebration. She arrives by Uber, does not drink, and drives him home in his car. His new car. It’s a mostly fun night and it’s a cool car, so when he asks her to spend the night, she agrees, but the sex is perfunctory: they both orgasm, but it isn’t tremendously amazing, and he falls asleep immediately after. She isn’t that tired, so after she gets him settled, checks the fridge for food, notices it is kinda scary, she snags his car fob, door key, leaves a note and arranges to be let back in with the concierge when she leaves the building (“I”m gonna surprise him with breakfast but he has fuck all in the fridge. Will you let me back in so I can run to the store?”). She feeds him breakfast in the morning, he’s a little stunned and confused but not too hung over, and she clears out before he can try for round two. He goes to work.

When he gets out of work that afternoon (early!), he gets a phone call from Kara who wants to meet him. They meet for an early dinner and have The Discussion. They don’t eat much, it lasts about two hours and is mostly conducted in intense whispers. They go over what happened when Kara left. She makes really good points about how she left because he completely ignored her AND he was doing a lot of yelling (he was _definitely_ a bad boyfriend during this period and arguably verbally abusive). “You were abusive, but I get that it was a time and place thing, so I’m prepared to take you back on some conditions.” He point outs how he wanted to quit so he could spend more time with her and she rejected that because she wanted him making more money so he went out and did that (kind of a whiny, passive aggressive thing going on, but basically valid). “I don’t care what the conditions are, because I don’t trust you.” Zach says she’s either too stupid to understand the consequences of her desires (go make me a bunch of money oh look you are a BEAR when you are working that hard) or unreliable during the inevitable down times when engaging in high risk high reward activities. She argues that he can give her both time and money now so why not? Wouldn’t he be offering that deal to any future partner? He says, at least he won’t know going into it with one of them that they’ll dump him in the crunch. He wants/needs at least the hope/illusion that someone loves him enough to stick it out through the hard times. Nobody cries and everyone feels horrible after. When they leave the table, Zach notices a piece of paper that Kara got out when she started talking about her conditions if they got back together. She has already left the restaurant, so he brings the piece of paper with him, but does not read it immediately.

Vanessa has dinner with Daniel Lee. He’s looking for a contractor to come in and help rescue EstatePro. Vanessa wants to know the details before she discusses money or anything else. EstatePro is a bunch of drastically simplified accounting and report generation software, combined with contact management, calendar management, and some pieces oriented towards making event planning and security management work better — that part is probably  mostly a ticket system. And the whole thing has extremely heavy security and encryption and is sold as part of an extremely expensive subscription service, with the intention of replacing bespoke software and off-the-shelf business software used by household staff of the uber rich. I haven’t decided if the project is the work of one or more tech billionaires who got disgusted with what was available and treated it as a potentially money-making sideline — sort of like Corbis was for Bill Gates and art. While the product partially exists (it was somebody’s bespoke system originally), the feature list has gotten huge and there are management problems because the people deciding the features haven’t hired people who can clearly communicate tradeoffs. Also, one of the higher level people in the group developing the service is a loyalty hire by the/a person/people funding the project and is not very competent.

In more or less the same fog that resulted in the new car, Zach buys a beautifully renovated house. His furniture from the one bedroom is lost in the new place, but he can’t figure out how to furnish it, beyond a home theater that he has installed and an insane gaming room. But he does want to have a big party to celebrate his beautiful new life, so he hires a caterer that will bring in tables and so forth. He tries to take Vanessa out to dinner, but she counter-proposes a walk.

She gets a summary of what he has been doing (buying stuff, basically, and a very brief summary of what happened with Kara), and he comments that it’s great he doesn’t have furniture yet, because it would get ruined at the party, anyway. She disagrees with that, and he admits he has no idea what to get. She pries out of him that an interior decorator was pushed at him, but he finally balked at that point. He suggests that she could help him out. She declines. He names someone who she has helped pick out a sofa for in the past. She says, there’s a big difference between a sofa and a couple arm chairs and enough furniture to fill up a Seattle Box. He’s trying to get this done for free, and while setting up a household is fun, the scale of this is kind of huge, he is not at all clear about what he wants and he tends to argue with her suggestions (she asserts that people would drink less and behave better in a well-furnished space and he doesn’t believe her, focusing on the greater potential for damages). Despite this disagreement, they wind up back at his place, and have a much better second overnight. (He does have bedroom furniture, altho there is a lot of spare space around it.)

Zach finds the piece of paper Kara left at the restaurant in the hours before The Party. He reads it, and realizes that Kara was wildly incompatible with what he wanted from his future in a laundry list of ways that he had been in denial about. He is shocked, but no longer in any doubt about his decision not to take her up on the idea of getting back together. The Party: it’s fun, Vanessa attends but leaves early. Zach notices her leaving and tries to get her to stay. She says she has something scheduled in the morning. When the party winds down and the caterers have cleared out, leaving nothing behind except some wine stains on the carpets, Zach closes the door, arms the alarm system, sits down on the floor and cries. He doesn’t even know why he is crying, but everything feels empty to him. Kara is gone. Vanessa is not at all a sure thing. His Big Idea has succeeded and moved on without him. He’s in a beautiful but empty, expensive house, with a lot of expensive toys, and no one to share them with. And no idea what he is going to do with himself when the transition is over.

Third third: Vanessa accepts the 6 month gig at EstatePro. She immediately starts assembling the feature list and methodically working with the existing team to establish priority order on the feature list and produce a believable schedule. Antics ensue, initially with the loyalty hire who refuses to either make decisions or produce working code that he has promised within various time frames, all missed.

Zach decides that he needs some useful advice. He talks to his mom about what happened with Kara; he discovers mom absolutely HATED Kara and has been having trouble concealing her glee about how Kara dumped her son in the crunch. Kara’s list included No Children. Nancy is not surprised. Zach also talks to a bunch of his friends. Some of them think he should have restarted things with Kara (“She’s hot”) but Zach does not elaborate why he isn’t going to (“Dude, your girlfriends either cheat on you, rob you blind, or both”). Some of them try to set him up with other women. They all agree that he has a problem in terms of finding someone to date that he can be at all confident is dating him and not his new wealth. His brother suggests he go talk to Vanessa about this (“She’s already done this. She probably has something useful to say.”) Zach does not tell anyone at this point that he’s feeling serious about Vanessa; he also doesn’t tell Vanessa about what just happened with Kara.

While out on a day hike that Zach suggests but Vanessa picks the trail, Vanessa declines to tell him how to live his life, and finds herself extremely bored doing the same thing socially that she is at work, (“What is the priority here? Identify it, make a plan, execute”). He is not looking for someone to project manage the Finding Myself process. Furthermore, he is incredibly embarrassed to realize how out of shape he has gotten. Despite talking at cross purposes for some of the hike, they really enjoy being together, being in the woods, swimming in the extremely cold Lake 22, stopping for beer and burgers on the way back. He spends the night at her place, and the next day he goes back to his gym and sets up a twice a week appointment with a personal trainer, who recommends a nutritionist to him, and he starts biking again.

Vanessa escalates the issues with the lack of prioritization, lack of stable feature set, and incompetence of the loyalty hire. Daniel freaks out, but does not attempt to stop her. Vanessa’s attitude: Fire Me. Please. This is actually worse than I thought it would be. I would rather be poor. Whoever is at the top of the food chain listens to her, makes a bunch of decisions, and signs off on a schedule. The loyalty hire is sidelined. Everyone resumes working with renewed energy and optimism.

Zach discovers that Vanessa is now almost entirely unavailable, other than for an occasional lunch or dinner or an hour walk in the evening, to wind down before going to sleep. She’s having trouble focusing on what he wants to talk about and is too tired for anything but the briefest sex. He is starting to understand what Kara went through. His friends are not seeing them together. In combination with her unavailability even on weekends, they wonder if Zach has invented the relationship (possible jokes about imaginary girlfriend). Because the time commitment is defined, and because he doesn’t want to be a hypocrite, he sticks it out. He also writes an apology letter to Kara.

Work hours stabilize at EstatePro as they start producing according to the new schedule. She gets some weekend time, and rather than devote it 100% to her older friends, she works with Zach to find a percentage that will make him feel like he’s important to her. Where possible, she starts bringing him along to meet her older friends and he obviously includes her with his friends. The mid-week evening walks become a combination of how was your day combined with reviewing past history and tentatively figuring out whether they have comparable future goals.

Once Zach settles into the new fitness routine and isn’t completely wiped out by it all the time, he decides he should just GTD the furnishing of the house. As soon as he goes down the list of rooms and starts thinking about what goes where, he realizes furnishing the house has implications for the future. Are there going to be children in this house? He brings the topic up with Vanessa, and doesn’t time it well. (“Really? You want to know if I ever want to have kids with you so you can furnish your house appropriately? I feel like this is backwards somehow. Also, I am really not in the mood for this.”) Once they calm down, they discuss The Kid Thing: Zach belatedly realizes that (a) Kara actually didn’t want kids, but wasn’t going to tell him that, (b) HE cannot imagine not having kids, altho he’s negotiable on how many. (“Vanessa:  How come every time we have a relationship conversation, you bring Kara up?” “I was with her for years, and I thought about my future in terms of being with her. Wow. That came out wrong. I love, you, okay? I’m thinking about the future with you. I’m asking you about kids. I want to know what you want. I want kids. I really hope you do too.”) Vanessa talks about her siblings starting families and how excited she is about that. She does not want more than two, but is otherwise negotiable. (“But do not furnish a child’s room now. That’s just nuts.”) Zach decides he can put a rocking chair and a single bed in the putative nursery and use it as a guest room until something else happens.

Vanessa’s contract had a bonus structure. She was committed to 6 months at straight pay, enough to make it very worthwhile (low order 6 figures). If the project was not complete, each side had the option to bail at 6 months, but if she stayed on, she continued at the same pay rate, until somebody called a halt. There was additional bonus for project completion at 6 months, and the bonus decreased to zero over the course of another year. They have a deployable product at a little over 7 months, and Vanessa and the team feel confident the team can complete the work without her participation, so Vanessa takes a reduced bonus at 7 months and gets the hell out (total take around half a million dollars, less than the potential maximum of a million, but more than she was expecting going into it with the problems Daniel Lee had described to her). Vanessa and Zach have dinner to celebrate the end of that (at least for now; they may call her back in in the future because they liked her, and they’ll be telling everyone how great she was). Vanessa is happy she took the job. Zach is less enthused: he would have liked to have had the time together, and when he compares the amount of money he spent furnishing his place vs. the amount she earned, he feels like she didn’t earn that much. Vanessa’s explanation is because if she turns out to have miscalculated on how much money she needs to live on/she makes disastrous investment errors, this is the kind of gig she wants to take so she can work part of the time and not work part of the time. Also, dude, let’s not lose track of how much a few hundred thousand means to me, just because it means very little to you.

He asks her to move in with him; they aren’t spending any nights separately any more, and they are Meeting Each Other’s Family/Spending Holidays Together. Everyone is getting nagged about picking a date and/or when they are going to have kids. She points out that there is a problem here, in terms of how much she makes/has vs. how much he makes/has. He just looks at her, laughs, and introduces her to his brother and brother-in-law. They are quite vehement in their opinion about how to handle this situation, and it moves the debate out of the male/female provider/domestic servant realm. When they start to wind down, Zach says she shouldn’t worry so much because they’ll just hire a lot of it done anyway, and she’s set a standard of not accepting the management hassle. After duly noting how happy she is that he even recognizes that there is a management hassle associated with hiring help (“Ha! You should hear my mother on the subject.”), she retorts that if they hire that many people, his money won’t last, and they’re off again.

When they revisit the question, they hammer out some basics: separate accounts, separate decision making. They’ll both fund education trusts for children. They agree to keep the debt to a minimum, and the lifestyle from creeping too badly. She’s not allowed to stop him from spending his money and having fun with it (“If I run out, I’ll just enjoy being poor. You know, like you.” Vanessa glares at him.). He is not allowed to expect her to fund or even participate in a lifestyle she is unhappy with. No one takes a high time commitment job without consulting first. They can’t _both_ have high time commitment jobs while the kids are young.
Then they look at each other and go, Oh My. We can actually do this. Whose mom do we call first with the news?

Tools: random dates, college degrees, names

I used these tools to fill out the large scale details on the friends-and-fam.

http://www.ssa.gov/OACT/babynames/index.html

Popular names by gender and year. I tried to stay away from the most popular names, names I believed implied race/ethnicity that wasn’t applicable to the character, or that struck me as implying the families were more religious than they actually are (which is not very). I did some searching on LinkedIn and Facebook, to make sure that the name combinations I picked weren’t real people who were the only people who had a given name combination, or which generated enormous numbers of hits.

Birth years were calculated. The main characters are supposed to be millenials, and their friends and coworkers (mostly) are also. I calculated parents age and sibling ages to fall within what I believe are typical patterns for boomer parents/millenial children. I then researched whether the fathers would have had to worry about the draft, and concluded that they probably thought about it while in high school, but given their birth year, it turned out not to matter.

The _general_ location is Pacific Northwest. However, I have not yet nailed down where everyone went to high school/college. I used this to pick common surnames, along with an FB group I am on that has members from my own high school.

http://ngm.nationalgeographic.com/2011/02/geography/usa-surnames-interactive

I used this to come up with month/day of the month for birthdates and marriage dates. I threw out some dates, because I didn’t want a character born on September 11, and I didn’t want more than one character with a birthday that fell within one week of Christmas. I got one date twice, and threw out the second instance, so I wouldn’t have two characters in this group that shared a birthdate. I do want to point out that these all _reduced_ the believability of this group. Two characters sharing a birthday would have been expected with this size group.

http://www.springhole.net/writing_roleplaying_randomators/dates.htm

I used this to help me pick college majors and careers for characters:

http://college.usatoday.com/2014/10/26/same-as-it-ever-was-top-10-most-popular-college-majors/

I did not want to write something that suffered from relentless whiteness or traditional gender roles/occupational choices. While some diversity is specific to the PacNW (some scandinavian last names in there), I wanted to reflect some of the diversity that I saw when I was working in tech in the area, and which I see in my town now, in part because a lot of the families living here are also working in tech.

NotAB: Cast of Characters

Missing: relationship statuses for Partners at Indices and Vanessa’s friends, high schools and places of birth for some parents/spouses [babies have been added]

Our Hero: Zachary Douglas Todd, b. 4 October 1983 (Northwest Hospital in Seattle), graduated high school (Shorewood) 2002, college 2006 (UW computer science and engineering). Family home is in Innis Arden.

His Mom: Nancy Susan Douglas Todd, b. 23 December 1957, graduated high school (Burlington-Edison) 1975 and college (Western Washington in Bellingham, State College when she entered, University by the time she graduated, education) 1979, m. 12 July 1981 (so she has the classic screwed up birthday problem) [I think she grew up in Skagit or Whatcom, and her father worked in an industry that was disappearing by the time she came along, as some sort of manager, and her mother was a nurse. She got a teaching job in Shoreline School District and met her husband at a night club, probably Parker’s. They bought their house in Innis Arden in August 1986].

His Dad: Gregory “Greg” Vance Todd, b. 12 March 1954 (parents living in Richland in the military city, born at Kennewick General Hospital), graduated high school 1972 (Richland High School), college 1976 (WSU, accounting), m. 12 July 1981 (because he was born in 1954, never eligible for draft)

His brother: Nicholas Dylan Todd, b. 5 January 1985 (Northwest Hospital in Seattle), m. August 16, 2014,  high school 2003 (Shorewood), Bastyr Exercise Science degree 2008, personal trainer (certification?), they are trying to adopt, they will succeed and bring their baby home in the fall of 2015.

His brother’s husband: Steven Nathan Clark, b. 6 March 1983, m. 16 August  2014, graduated 2005 from UC San Diego in Computer Science, currently employed at Amazon, met Nicholas at a gaming group before the Amazon job

Zach’s Ex-Girlfriend:Kara Nicole Young, b. 28 April 1986

Partner in Indices 1: Prem Gupta, b. 24 March 1991 in the US to recently immigrated parents

Partner 2: Sarah Nguyen, b. 11 April 1980 in the US to parents who immigrated in 1975

Partner 3: Victoria “Tori” Bergstrom, b. 20 July 1984

Partner 4: Joshua “Josh” Cordell, b. 2 June 1975

Our Heroine: Vanessa Ellen Baker, b. 14 October 1982 (UW Medical Center/Hospital) (family calls her Nessa; older friends call her Van; she used Vanessa at work) (close birthdays!), high school 2000 (Shorecrest), college 2004 (UW computer science and engineering) (pre-k, kindergarten and most elementary in Montessori) Family home is north of Hamlin Park, bought in summer 1992; before that they were renting in Maple Leaf, Green Lake, or similar.

Her Mom: Sharon Lynn “Shari” Cooper Baker, b. 24 May 1957, graduated Roosevelt High School 1975, m. 7 July 1979, series of nursing degrees, ending up as a nurse practitioner (CNA or similar, LPN, LPN-RN bridge program, RN-Master’s of Nursing, using a variety of schools, and getting a bachelor’s as well in order to do the RN-Master’s bridge at the UW or similar), grew up in Maple Leaf

Her Dad: Robert Irving  “Irv” Baker, b. 3 April 1954, m. 7 July 1979 (because he was born in 1954, never eligible for draft), Roosevelt high school 1972, college 1976 (UW, business), went back for an MBA (1990-1), grew up in View Ridge

Her brother: Terrance John “TJ” Baker, b. 16 September 1980 (UW Medical Center), m. 28 June 2014, high school 1998 (Shorecrest), cosmetologist, owns a salon, rents chairs (I’m thinking he went to Shoreline Community College in the early 2000s, probably starting with the cosmetology degree right out of high school and then adding business classes until he got a certificate, taking more classes when things were slow at the shop, alternatively Gene Juarez) The move to the family home was timed perfectly for him, as he was about to age out of Montessori and needed a middle school option. TJ and Kimmy got married with the expectation they would immediately start a family. They will be expecting twins in July 2015.

Terrance’s wife: Kimberly Anne “Kimmy” Larson, b. 5 August 1984, m. 28 June 2014, graduated high school 2003, UW accounting degree and post program to get enough to sit for the CPA exam, CPA passed 2008, in a tax practice focusing on high net worth individuals

Her sister: Brittany Grace Baker, b. 17 November 1985 (UW Medical Center), m. 26 June 2010, high school graduation 2004 (Shorecrest), EMT (North Seattle College), she aspires to get into the Harborview paramedic program. She spent the fewest years in Montessori, and the most years in public school, starting in 1st or 2nd grade. Once TJ and Kimmy are expecting, Brittany succumbs to increasing pressure from Mitch, and her mother, and they start trying to have a baby. She will be expecting a single child in February 2016.

Brittany’s husband: Mitchell Ryan “Mitch” Adams, b. 18 February 1984, m 26 June 2010, police officer (2 year degree Shoreline Community College Criminal Justice, got hired, went to BLEA etc.)

Friend 1: Holly Chen, b. 28 March 1983

Friend 2: Erin Benson, b. 8 September 1982

Friend 3: Marisa Schuyler, b. 7 June 1980

Friend 4: Jeffrey Bingham, b. 20 March 1982

Coworker at EstatePro: Daniel Lee

Loyalty Hire at EstatePro:

Finance Team

Realtor: Suzanne Armstrong, b. 18 December 1965
Estate lawyer

Not a Billionaire: Plot

THIS NOVEL DOES NOT EXIST. But if it ever exists, this probably would constitute major spoilers.

I am terrified I might inadvertently commit literary fiction here, so I’ll just say up front I’m aiming for a traditional contemporary romance novel (heterosexual, HEA) but might miss because I suspect it is closer to a bildungsroman, if one of those could be about a class transition as opposed to a becoming-an-adult theme.

Traditional contemporaries suffer from a where’s-the-conflict problem, and I’ve got that problem. I think of the main conflict as values/judgment and the surface conflict as timing/preference. Subtle conflict can get swamped by larger issues, so the two characters are going to be as alike as I can make them otherwise:

They both have a tech degree (computer science, almost certainly), worked in the tech industry (probably PacNW/Seattle specifically, because I know it the best), recently retired (she’s been retired slightly longer, with less money and still works occasionally — kind of the Early Retirement Extreme version), early 30s, stable family of origin/extended family (and not huge either: so basically 1 or 2 siblings each, similar in age, college educated, with families and job, parents living, possibly grandparents living, small number of uncles and aunts, etc), parents have at least some college education (so this isn’t blue collar, altho they may not all be doctors and lawyers), no nutty religions anywhere in sight, no severe mental illness or disability in the closer extended family — these two are probably the nerdiest in their respective clans and they are probably also unusual in that they are both quite money-focused.

The main conflict is that she doesn’t want to move too far from her origins, and he does. She recognized the kind of distortion in her life that would accompany wealth/retirement and did her best to plan for it/step off at a level she was comfortable with. He did not, mostly because he didn’t think it through and he was doing something that other people were telling him he should want to do.

They met originally at a startup that was successful enough for her to retire (at least for Early Retirement Extreme definitions of retirement). They did not arrive at this startup at the beginning, so they have less burnout and less money than some of the earliest participants and they have some appetite for another. He was in a relationship when he was at this company; she was not. They worked together altho not very closely and were friendly, but this isn’t a Identified True Mate On Sight story. Previous to this company, he had internships while in college and then worked at an established company for a couple years, then at a late phase startup that was acquired by a larger company. His previous relationship started in this time frame, and survived his next employer, a startup that he was in on early and failed relatively quickly. He thinks about retiring, but his significant other is opposed (not a fan of the high asset/low run rate life style). He has a startup idea of his own, and some buddies and 3-4 of them put together an app/cloud service (a document indexing service cloud/app/subscription service). However, it takes up all of his time and a fair amount of the money he had from the previously successful startup, and during a rocky period in the middle of it (when the seed money is running out and they are starting the pivot to the corporate facing version of their service), the girlfriend bails out on him.

He has a bad period of wondering if he should have done this at all, thinks about the money he has already sunk into this startup, considers giving up and taking a stable job at a more mature company (he has offers). He talks this over with friends, including Our Heroine and he is surprised that she is not advocating any particular position, but instead poking at him to understand himself better and what he wants. He isn’t really used to this, but decides to double down. He and his buddies experience substantial success post-pivot and are able to sell out to an investment group that keeps them around for 18-24 months of transition.

When the deal is done (but before the transition commitment is complete), he goes out with the partners and a few other friends. He invites Our Heroine as his date for the evening and they (not the crowd, just the Couple) wind up at her place for the night. She makes him breakfast the next day, and seems pleased with the rushed, somewhat drunken previous night, but when he probes for expectations, she indicates she thought this was I Need A Date crossed with Rebound, and is happy to continue as Just Friends. He is simultaneously relieved and disappointed and confused, mostly relieved because there is still a lot to do.

During the transition period, he starts to have more time on his hands. The ex-girlfriend attempts to get back together with him, and there is an extremely unpleasant discussion with her. She makes really good points about how she left because he completely ignored her AND he was doing a lot of yelling (he was _definitely_ a bad boyfriend during this period and arguably verbally abusive). And he should point out how he wanted to quit so he could spend more time with her and she rejected that because she wanted him making more money so he went out and did that (kind of a whiny, passive aggressive thing going on, but basically valid). Conclusion should be along the lines of, he says that while he can understand her perspective, he can’t _trust_ the person that he understands her to be: she’s either too stupid to understand the consequences of her desires (go make me a bunch of money oh look you are a BEAR when you are working that hard) or unreliable during the inevitable down times when engaging in high risk high reward activities. She quite tearfully argues that he can give her both time and money now so why not? Wouldn’t he be offering that deal to any future partner? He says, at least he won’t know going into it with one of them that they’ll dump him in the crunch. He wants/needs at least the hope/illusion that someone loves him enough to stick it out through the hard times.

Over the next period of time, he mopes about the state of his life and relationships. He thinks about Our Heroine during this period, and spends some time with her but is evasive about what is going on in his head, while discussing the situation with the ex- with a married sibling, also his mom (who he discovers absolutely HATED the ex-girlfriend and has been having trouble concealing her glee about how the ex- dumped her son in the crunch), and one or more other friends (whose advice ranges from, give her another chance she’s hot, from the guy who is always being cheated on, to glad you found some spine).

These conversations, in conjunction with a lot of friendly warnings that now that he has so much it will be hard to figure out who wants him for him, cause him to completely freeze on dating. He’s not progressing the relationship with Our Heroine because he doesn’t trust his own judgment/is terrified. She’s not pushing the relationship because she doesn’t really want to be with someone who isn’t enthusiastic enough about her to push.

He’s past an age where he just wants to sleep around, and can’t quite figure out how to solve his dilemma, so he just doesn’t bother. A fair number of people pressure him to start dating again, setting him up with people, introducing him at parties and he resists. Our Heroine is happy to come to his parties and hang out with him in groups, tends to drink less than everyone else, and while she is a lot more available than most of his friends and acquaintances for mid-week activities (maybe they go on a couple day hikes), she doesn’t stay out very late, and her weekends are frequently booked up far in advance, so while they are seeing each other fairly regular and even having regular sex and overnights, the circle of friends is not correctly perceiving what is going on (they see him without her about as often as they seem both of them, and they don’t really believe that all the rest of this mid week stuff is happening). Possible jokes about imaginary girlfriend.

He has been hooked up with a wealth management team, gets a personal trainer and adopts some Active Hobbies (probably mountain biking and/or road biking, dabbling in other things, but I don’t want this guy to be so well put together that he hooks up with an ultimate frisbee team and I don’t want him to be a rock climber either), when he notices he is gaining weight and generally feeling like crap from too much partying. He is also embarrassed by their relative stamina on day hikes and similar.

The wealth management team does some things beyond helping him decide on a stock selling plan and diversification strategy. They get him to put together a will/trust, and hook him up with a real estate agent. He’s okay with doing the will/trust (on screen conversations at least on the phone probably in person with his parents/siblings/etc. in the course of doing this, particularly for living will/medical power of attorney parts). He’s less okay with the real estate agent and stalls for a while, but the agent is persistent and at some point, he has enough time and is sufficiently caught up on other basic needs that he sees a house he absolutely adores and buys it. The agent then attempts to hook him up with an interior decorator, and he acknowledges that the house is crazy empty with just the stuff from his 1 bedroom apartment, but cannot bring himself to make decisions about what to put in the house. He has a gorgeous bedroom picked out by/with the ex-girlfriend, and a kitted out kitchen because he is able to cook, but there’s basically Ikea couch and similar in the sparsely populated living room and nothing in the dining room at all (there’s an eat-in area in the kitchen). He orders up a home theater. He has an amazing game system and buys supportive furniture, and has a bunch of gamers over for messy parties (is this computer gaming, board gaming, poker party, all of the above?). One of his arguments AGAINST buying nice furniture is how trashed the place is after a night of movies, games, cosplay all fueled by kegs, a staffed bar and solo cups.

He attempts to recruit Our Heroine to fill in the empty spots: pick out furniture, deal with caterers, etc. She balks. She isn’t particularly interested in the hassle, which pulls him up short, because he had gotten the impression that this was something that All Women Wanted/Did or at least did when they were coupled up, and he can tell from her life that she is quite capable of it. When she declines, he points out that he knows she has helped other people buy sofas etc. She points out that he has referrals to interior decorator etc. which he has declined. He’s trying to get this done for free, and while setting up a household is fun, the scale of this is kind of huge, he is not at all clear about what he wants and he tends to argue with her suggestions (she asserts that people would drink less and behave better in a well-furnished space and he doesn’t believe her, focusing on the greater potential for damages).

She is willing to go out on at least some dates, spend the night, text and call casually on a mostly daily basis, but doesn’t pressure for any commitment or change her FB relationship status (“it’s complicated”, which it has been the entire time he has known her, and he has known about other people she has dated and stopped dating through that time frame). He can’t figure out what any of this means. He also sees himself as low-priority for weekend scheduling, and they talk about why that happens (he is one of her newer friends — most of her friends have been part of her life for a decade or more; he tends not to schedule as far out as most of the rest of her social circle does, so he loses to prior commitments) and come up with some workarounds (we will spend these Friday or Saturday nights as a couple, regardless, and if that means with her friends or with his friends due to later commitments, that is okay).

Heavy handed moralizing here by the author: up through the slightly more mature and ultimately successful startup job, Our Heroinel and Our Hero were quite similar. However, her decision to “retire” caused her to go through a Now What/What is the Good Life/Time to Grow Up process that he did not go through because he was immersed in an extremely time consuming startup that had a lead role in. Now that he has pulled back from the day-to-day/retired himself, he is going through a process she has mostly completed. They are different in several key ways: the above obvs, but also he is substantially wealthier than she is and he has had a taste of wheeling/dealing/hustling that she never has. Her life, world and perspective are drastically simplified by having fewer options and clearer priorities, so while he is overwhelmed by choice and uncertain how to make those choices, she is decisive and has a ton of spare capacity to spend on thinking about how other people do things/what other people are currently thinking and feeling. He would _love_ to have someone take over a lot of this, and figures she’s a great choice for it (she’s already done it once and knows how). She figures that if he’s gonna outsource it, he should pay professionals, but she also thinks he should work through the process himself because that’s what she did. Ultimately, he will need to figure out what his own priorities are (the important part of the process) and then outsource selectively/consciously (not just: live my life for me).

As his transition period is winding up, she is asked by a former co-worker (of both of them) to help out on a niche app/cloud service that he has been working on. It is supposed to be a 6 month commitment, but it goes long. (The service is a bunch of drastically simplified accounting and report generation software, combined with contact management, calendar management, and some pieces oriented towards making event planning and security management work better — that part is probably  mostly a ticket system. And the whole thing has extremely heavy security and is sold as part of an extremely expensive subscription service, with the intention of replacing bespoke software and off-the-shelf business software used by household staff of the uber rich. I haven’t decided if the project is the work of one or more tech billionaires who got disgusted with what was available and treated it as a potentially money-making sideline — sort of like Corbis was for Bill Gates and art). One of the higher level people in the group developing the service is a loyalty hire by the/a person/people funding the project and is not very competent. Our Heroine winds up spending a fair amount of time trying to get the requirements and priorities better defined and a reasonable schedule assembled and communicated above/around the problematic person. She is well-compensated, but happy to leave after somewhere between 6 months and a year.

Our Hero is frustrated at her months of unavailability right when he’s got a ton of time on his hand, but he doesn’t dump her, partly because he doesn’t want to be a hypocrite, partly because it is a defined time commitment. But he also sort of thinks, why the hell are you bothering to do this when the payoff won’t be that good and it wasn’t your idea and so forth. Our Heroine’s explanation is because if she turns out to have miscalculated on how much money she needs to live on/she makes disastrous investment errors, this is the kind of gig she wants to take so she can work part of the time and not work part of the time. Also, dude, let’s not lose track of how much a few hundred thousand means to me, just because it means very little to you.

Meanwhile, because she’s just not around and he needs something to do with himself, he turns the house into a Project and just GTDs the whole thing. This actually can combine with the debate about how much a million is worth, when they look at how much she made and how much he spent during the same period of time.

When her gig is done, and his house is furnished, she’s feeling exhausted and relieved to be done working for a while, at the same time she’s got a ton of offers because she Rescued a Near Disaster. They decide they actually get along really well, despite the values differences and the sex is good at least when they’ve been getting enough sleep. He mostly comes around to her way of thinking (keep taking jobs part of the time and not working part of the time) and she decides she’s prepared to participate in his more expensive lifestyle, as long as he doesn’t force her run rate up.

Something like the end, possibly with babies.

I’m still debating about whether I want to flip the genders (make her be the one who overshoots on the lifestyle and then freaks out). But fundamentally, I really want her to be the smart one, so I think not.